Throughout the regular season and playoffs, teams wore a patch celebrating the turn of the millennium (see above).

Beginning this season, teams would earn one point for an overtime loss in the regular season instead of zero. It was hoped that this change would stop teams from playing very defensively during the overtime in an effort to guarantee the single point from a tie. The number of ties had been going up for some years and the NHL was hoping to counter this trend, and in fact did so quite successfully with this rule change.[1]

This season was also the start of the NHL's partnership with ABC, who would televise a few regional games every season, as well as games three through seven of the Stanley Cup Finals. ESPN, who with the ABC deal renewed their contract with the NHL, continued to show regular season and playoff games as well as the first two games of the Stanley Cup Finals.

Two upsets occurred in the first round as seventh-place Pittsburgh defeated the second-place Washington Capitals in five games and eighth-place San Jose defeated the first-place St. Louis Blues in seven games. Both Pittsburgh and San Jose lost in the second round to end their seasons. In the East, fourth-place New Jersey Devils defeated fifth-place Florida Panthers, third-place Toronto Maple Leafs and first-place Philadelphia Flyers to advance to the final. In the West, the second-place Dallas Stars defeated the seventh-place Edmonton Oilers, eighth-place San Jose Sharks and the third-place Colorado Avalanche to advance to the final.